Reductive Cross-Coupling of Vinyl Electrophiles

Xiaobo Pang; Xuejing Peng; Xing-Zhong Shu

doi:10.1055/s-0040-1707342

Synthesis, Table of Contents

Synthesis 2020; 52(24): 3751-3763
DOI: 10.1055/s-0040-1707342

short review

Reductive Cross-Coupling of Vinyl Electrophiles

Authors

Xiaobo Pang
Xuejing Peng
Xing-Zhong Shu ∗

State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, China Email: shuxingzh@lzu.edu.cn

Abstract

All articles of this category

Abstract

The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.

1 Introduction

2 Cross-Electrophile Coupling of Vinyl Electrophiles

3 Reductive Heck Reaction of Vinyl Electrophiles

4 Summary and Outlook

Key words

alkenes - cross-coupling - reductive coupling - cross-electrophile - Heck reaction - vinylation - nickel - cobalt

Full Text

References

References

1a Larock RC. Comprehensive Organic Transformations, 2nd ed. Wiley; New York: 1999
1b Álvarez R, Vaz B, Gronemeyer H, de Lera ÁR. Chem. Rev. 2014; 114: 1
1c Zweig JE, Kim DE, Newhouse TR. Chem. Rev. 2017; 117: 11680

2 For a review of the synthesis of alkenes see: Science of Synthesis, Vol. 47a and 47b. de Meijere A. Thieme; Stuttgart: 2009

3a Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PG. Wiley-VCH; New York: 1998
3b Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014

Recent elegant reviews, see:

4a Knappke CE. I, Grupe S, Gartner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem. Eur. J. 2014; 20: 6828
4b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
4c Weix DJ. Acc. Chem. Res. 2015; 48: 1767
4d Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
4e Lucas EL, Jarvo ER. Nat. Rev. Chem. 2017; 1: 65
4f Richmond E, Moran J. Synthesis 2018; 50: 499

5a Wurtz A. Ann. Chem. Pharm. 1855; 96: 364
5b Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 34: 2174

Some pioneering work:

6a Gomes P, Gosmini C, Périchon J. Org. Lett. 2003; 5: 1043
6b Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920
6c Wang S, Qian Q, Gong H. Org. Lett. 2012; 14: 3352
6d Cherney AH, Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2013; 135: 7442

7a Heck RF. Acc. Chem. Res. 1979; 12: 146
7b Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
7c The Mizoroki–Heck Reaction . Oestreich M. Wiley; Chichester: 2009
7d Oxtoby LJ, Gurak JA. Jr, Wisniewski SR, Eastgate MD, Engle KM. Trends Chem. 2019; 1: 572

8a Czaplik WM, Mayer M, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2009; 48: 607
8b Krasovskiy A, Duplais C, Lipshutz BH. J. Am. Chem. Soc. 2009; 131: 15592
8c Cao Z.-C, Luo Q.-Y, Shi Z.-J. Org. Lett. 2016; 18: 5978

9 Boyarskiy VP, Ryabukhin DS, Bokach NA, Vasilyev AV. Chem. Rev. 2016; 116: 5894
10 Xiao L.-J, Ye M.-C, Zhou Q.-L. Synlett 2019; 30: 361

11a Conan A, Sibille S, d’Incan E, Périchon J. J. Chem. Soc., Chem. Commun. 1990; 48
11b Durandetti M, Nedelec J.-Y, Périchon J. J. Org. Chem. 1996; 61: 1748
11c Cannes C, Condon S, Durandetti M, Périchon J, Nedelec J.-Y. J. Org. Chem. 2000; 65: 4575

12a Gosmini C, Bégouin J.-M, Moncomble A. Chem. Commun. 2008; 3221
12b Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435

13 Gomes P, Gosmini C, Périchon J. J. Org. Chem. 2003; 68: 1142
14 Moncomble A, Le Floch P, Lledos A, Gosmini C. J. Org. Chem. 2012; 77: 5056

15a Bassler DP, Alwali A, Spence L, Beale O, Beng TK. J. Organomet. Chem. 2015; 780: 6
15b Beng TK, Sincavage K, Silaire AW. V, Alwali A, Bassler DP, Spence LE, Beale O. Org. Biomol. Chem. 2015; 13: 5349

16 Cai Y, Benischke AD, Knochel P, Gosmini C. Chem. Eur. J. 2017; 23: 250
17 Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
18 Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
19 Johnson KA, Biswas S, Weix DJ. Chem. Eur. J. 2016; 22: 7399

20a Gu J, Qiu C, Qian Q, Lin K, Gong H. Synthesis 2017; 49: 1867
20b Qiu C, Yao K, Zhang X, Gong H. Org. Biomol. Chem. 2016; 14: 11332

21 Biswas S, Weix DJ. J. Am. Chem. Soc. 2013; 135: 16192
22 Liu J, Gong H. Org. Lett. 2018; 20: 7991
23 Liu J, Lei C, Gong H. Sci. China Chem. 2019; 62: 1492
24 Wang X, Ma G, Peng Y, Pitsch CE, Moll BJ, Ly TD, Wang X, Gong H. J. Am. Chem. Soc. 2018; 140: 14490
25 Lu X, Wang Y, Zhang B, Pi J.-J, Wang X.-X, Gong T.-J, Xiao B, Fu Y. J. Am. Chem. Soc. 2017; 139: 12632
26 Xu H, Zhao C, Qian Q, Deng W, Gong H. Chem. Sci. 2013; 4: 4022
27 Yan X.-B, Li C.-L, Jin W.-J, Guo P, Shu X.-Z. Chem. Sci. 2018; 9: 4529

28a Ye Y, Chen H, Sessler JL, Gong H. J. Am. Chem. Soc. 2019; 141: 820
28b Chen H, Ye Y, Tong W, Fang J, Gong H. Chem. Commun. 2020; 56: 45
28c Friese FW, Studer A. Angew. Chem. Int. Ed. 2019; 58: 9561

29 Gao M, Sun D, Gong H. Org. Lett. 2019; 21: 1645
30 Ye Y, Chen H, Yao K, Gong H. Org. Lett. 2020; 22: 2070

31a Noble A, McCarver SJ, MacMillan DW. C. J. Am. Chem. Soc. 2015; 137: 624
31b Yu W, Chen L, Tao J, Wang T, Fu J. Chem. Commun. 2019; 55: 5918
31c Zhou Q.-Q, Dusel SJ. S, Lu L.-Q, König B, Xiao W.-J. Chem. Commun. 2019; 55: 107

32a Cherney AH, Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365
32b Suzuki N, Hofstra JL, Poremba KE, Reisman SE. Org. Lett. 2017; 19: 2150
32c Hofstra JL, Cherney AH, Ordner CM, Reisman SE. J. Am. Chem. Soc. 2018; 140: 139
32d DeLano TJ, Reisman SE. ACS Catal. 2019; 9: 6751

33 Ackerman LK. G, Anka-Lufford LL, Naodovic M, Weix DJ. Chem. Sci. 2015; 6: 1115
34 Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
35 Liu J, Ren Q, Zhang X, Gong H. Angew. Chem. Int. Ed. 2016; 55: 15544

36a Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486
36b Rosen BM, Quasdorf KW, Wilkson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
36c Yamaguchi J, Muto K, Itami K. Eur. J. Org. Chem. 2013; 19
36d Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
36e Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
36f Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344

37 Jia X.-G, Guo P, Duan J, Shu X.-Z. Chem. Sci. 2018; 9: 640

38a Duan J, Du Y.-F, Pang X, Shu X.-Z. Chem. Sci. 2019; 10: 8706
38b Pan F.-F, Guo P, Li C.-L, Su P, Shu X.-Z. Org. Lett. 2019; 21: 3701
38c Tian Z.-X, Qiao J.-B, Xu G.-L, Pang X, Qi L, Ma W.-Y, Zhao Z.-Z, Duan J, Du Y.-F, Su P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 7637
38d He R.-D, Li C.-L, Pan Q.-Q, Guo P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 12481

39 See ref 2 and: Preparation of Alkenes . Williams JM. J. Oxford University Press; Oxford: 1996
40 Pearson RG, Figdore PE. J. Am. Chem. Soc. 1980; 102: 1541

41a Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 46: 5743
41b Do H.-Q, Chandrashekar ER. R, Fu GC. J. Am. Chem. Soc. 2013; 135: 16288
41c Liang Z, Xue W, Lin K, Gong H. Org. Lett. 2014; 16: 5620

42 Arendt KM, Doyle AG. Angew. Chem. Int. Ed. 2015; 54: 9876
43 Chen H, Sun S, Liao X. Org. Lett. 2019; 21: 3625
44 Qiao J.-B, Zhao Z.-Z, Zhang Y.-Q, Yin K, Tian Z.-X, Shu X.-Z. Org. Lett. 2020; 22: 5085

45a Zhang Y, Rovis T. J. Am. Chem. Soc. 2004; 126: 15964
45b Malapit CA, Bour JR, Brigham CE, Sanford MS. Nature 2018; 563: 100

46a Ackerman LK. G, Lovell MM, Weix DJ. Nature 2015; 524: 454
46b Olivares AM, Weix DJ. J. Am. Chem. Soc. 2018; 140: 2446

A review:

47a Ping Y, Kong W. Synthesis 2020; 52: 979

Selected work:

47b Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
47c Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722
47d Anthony D, Lin Q, Baudet J, Diao T. Angew. Chem. Int. Ed. 2019; 58: 3198

48 Ma T, Chen Y, Li Y, Ping Y, Kong W. ACS Catal. 2019; 9: 9127

Selected recent elegant work:

49a Li B.-J, Xu L, Wu Z.-H, Guan B.-T, Sun C.-L, Wang B.-Q, Shi Z.-J. J. Am. Chem. Soc. 2009; 131: 14656
49b Gärtner D, Stein AL, Grupe S, Arp J, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2015; 54: 10545
49c Li J, Knochel P. Angew. Chem. Int. Ed. 2018; 57: 11436
49d Li J, Ren Q, Cheng X, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2019; 141: 18127

50 Gomes P, Gosmini C, Périchon J. Tetrahedron 2003; 59: 2999
51 Amatore M, Gosmini C, Périchon J. Eur. J. Org. Chem. 2005; 989

52a Peng Y, Luo L, Yan C.-S, Zhang J.-J, Wang Y.-W. J. Org. Chem. 2013; 78: 10960
52b Xu X.-B, Liu J, Zhang J.-J, Wang Y.-W, Peng Y. Org. Lett. 2013; 15: 550
52c Luo L, Zhang J.-J, Ling W.-J, Shao Y.-L, Wang Y.-W, Peng Y. Synthesis 2014; 46: 1908
52d Peng Y, Xiao J, Xu X.-B, Duan S.-M, Ren L, Shao Y.-L, Wang Y.-W. Org. Lett. 2016; 18: 5170
52e Xiao J, Cong X.-W, Yang G.-Z, Wang Y.-W, Peng Y. Org. Lett. 2018; 20: 1651
52f Luo L, Zhai X.-Y, Wang Y.-W, Peng Y, Gong H. Chem. Eur. J. 2019; 25: 989

53 Li Y, Ding Z, Lei A, Kong W. Org. Chem. Front. 2019; 6: 3305
54 McGeough CP, Strom AE, Jamison TF. Org. Lett. 2019; 21: 3606
55 Burns B, Grigg R, Ratananukul P, Sridharan V, Stevenson P, Worakun T. Tetrahedron Lett. 1988; 29: 4329
56 Hou L, Yuan Y, Tong X. Org. Biomol. Chem. 2017; 15: 4803
57 Liang R.-X, Yang R.-Z, Liu R.-R, Jia Y.-X. Org. Chem. Front. 2018; 5: 1840
58 Arcadi A, Marinelli F, Bernocchi E, Cacchi S, Ortar G. J. Organomet. Chem. 1989; 368: 249
59 Ozawa F, Kobatake Y, Kubo A, Hayashi T. J. Chem. Soc., Chem. Commun. 1994; 1323
60 Saini V, O’Dair M, Sigman MS. J. Am. Chem. Soc. 2015; 137: 608
61 Ghosh T. ChemistrySelect 2019; 4: 4747
62 Ichikawa M, Takahashi M, Aoyagi S, Kibayashi C. J. Am. Chem. Soc. 2004; 126: 16553
63 Dounay AB, Humphreys PG, Overman LE, Wrobleski AD. J. Am. Chem. Soc. 2008; 130: 5368
64 Gao P, Cook SP. Org. Lett. 2012; 14: 3340
65 Hu P, Chi HM, DeBacker KC, Gong X, Keim JH, Hsu IT, Snyder SA. Nature 2019; 569: 703
66 Yu S, Berner OM, Cook JM. J. Am. Chem. Soc. 2000; 122: 7827
67 Zheng Y, Yue B.-B, Wei K, Yang Y.-R. J. Org. Chem. 2018; 83: 4867